


Strikingly Red

by blueelvewithwings



Series: Spanking Sunday [43]
Category: The Flash (TV 2014)
Genre: Caning, Dubious Consent, Initiation, Life Debt, M/M, Mob Boss!Len, Mobster AU, Servant!Barry, Spanking
Language: English
Status: Completed
Published: 2019-06-30
Updated: 2019-06-30
Packaged: 2020-05-31 02:49:19
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,305
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19416922
Author URL: https://archiveofourown.org/users/blueelvewithwings/pseuds/blueelvewithwings
Summary: Len is presented with his new servant, and of course, he has to test his endurance to see if he'll be any good.Prequel toHow Not To Treat Your ServantandAfter The Rain





	Strikingly Red

„This the new one, boss.“

Len looked up from the bills he was going over to see Mick shove a skinny guy to his knees in front of the desk, growling at him and looking at him with a threatening glare even though the skinny guy looked like he was scared enough to sink into the ground anyway.

For a moment, Len was confused, wondering what Mick meant. He couldn‘t be a new recruit, because Len would know about him, and he also wouldn‘t be made to kneel in front of him. So he figured it could only be one thing, and he smirked as he rose from his chair and approached the scared looking figure in front of him.

„So you‘re Allen‘s little boy, then? Took on a life debt to save poor old Daddy and then went into training camp to learn how to be good for me?“

Allen‘s boy swallowed visibly as Len‘s fingers glid along his jawline, but he nodded obediently and opened his mouth when Len rested his thumb on his lip, easily granting him entrance.

Well, this sure would be fun.

„What‘s your name then, Allen‘s boy?“ Len demanded, and even found himself merciful enough to take his thumb back out of the guy‘s mouth to allow him to speak. „Harvey or something, right?“

„It‘s Barry, Sir“, Allen‘s boy murmured with a little blush. He was cute, really. Len would love having him in his bed. But even being the Rogues, they didn‘t stoop as low as slavery, so he wouldn‘t be able to just command him into his bed. He‘d have to settle for coercion then and manipulate his new cutie into his bed.

„Barry. Hm, alright, let‘s see what you have.“

He waved at him to stand up, and Mick even took a step back to allow Barry to move. Obediently, Barry rose to his feet and stood in front of Len, hands clasped behind his back, gaze lowered. Like a good boy should be. Len was almost sad that he‘d been broken already, but Mick had told him that the Allen boy hadn‘t been much work to break in the first place, and that he‘d taken to his training like a fish to water, basically.

„Good. Now strip.“

Barry‘s eyes widened at that, but he obeyed nonetheless, not even questioning Len‘s order. He really must be adamant about protecting his sweet Daddy if he let himself be pushed that deep into servitude just to protect him. He wouldn‘t have needed to do that if only sweet goody two shoes Henry Allen would have agreed to work with them instead of staying on his boring, straight and legal path. Well, but Henry‘s refusal had gotten him Barry now, so that was good as well, he supposed.

He watched with seeming detatchment as Barry slowly took off his clothes, and Mick went to take his place in the corner that he always had when guarding Len in meetings. He didn‘t think that Barry would be any danger, but one could never be too careful. Also, from the way he was eyeing him, Mick didn‘t want to miss the show that was a cute twink stripping naked in Len‘s office, and Len certainly did not begrudge him that.

Once Barry was naked and all his clothes were folded neatly on the visitor‘s chair, Len nodded at him. „Bend over that chair. I‘m going to give you a taste of what it will be like if you disobey or fail to please me.“

Barry looked at him a little scared then, and Len could see his throat bob as he swallowed, but in the end, he nodded easily enough and turned around, bending over the chair to present his backside to Len.

„I hope I haven‘t displeased you yet, Sir?“

Len wanted to huff at him for speaking without being asked a direct question, but he knew he hadn‘t gone over the rules with him yet, and that he kept different rules from the ones the servants were taught back in the training center. So really, he couldn‘t punish him for this one yet.

„You haven‘t, boy. But make sure not to speak out of turn again.“

Barry bashfully ducked his head, but quickly nodded and settled into his position. Dear Lord, it was going to be beautiful to have this sweet piece of ass all for himself. Len gave his bubble butt a few spanks with his hand, just to see it wobble and dance, and then he reached for the cane that he had at the ready.

„So, boy… have you ever been caned before?“

Even without Barry turning around and looking at him, Len could see his eyes widen, and by the little aborted chuckle that Mick let out it sure must be quite the sight.

„I have not, Sir. May I… may I ask a question?“

Well, at least he had the good sense not to assume that he was allowed to keep talking after answering the question, that was good. It really did seem that he‘d taken well to his new role.

„Go ahead, what is it?“

„The cane… for what kind of infractions will it be, Sir?“ Poor Barry sounded a little scared, and Len couldn‘t help but to let a little smirk play over his face.

„Whatever kind of infractions I choose to punish like this. Mostly it will be larger things though, if you disobey me deliberately. For slip-ups and forgetfulness I might sometimes just use the ruler. But really, it will be whatever I feel like using. That answer your question?“

Barry nodded, then drew a sharp breath when Len slapped his ass again. „Yes, Sir. It does. Thank you for explaining.“ He didn‘t sound too happy with the prospect, but then again, he wasn‘t here to be happy.

Len walked around him to stand to the side, admiring the line of his body and the way his splendidly formed butt was pushed out at just the right angle, as if he were a natural.

„Now, I might not always tell you how many you are getting, but today we will keep it easy. It is just to show you, after all. Five strokes with the cane, and you will count.“

He waited for Barry‘s nod – very perceptive of the boy not to give a verbal answer – and then lifted the cane, all while grinning to himself. He‘d specified five strokes with the cane, but he hadn‘t told Barry how hard they would be.

Predictably, Barry yelped when the cane came down with full force and pushed him forward so harshly that even the stair started sliding over the carpeted floor and Barry had to take a step forward to keep his balance. At once, a nice deepily red welt was forming across Barry‘s porcelain white cheeks, and Len wanted to drink in that image and never look at anything else again.

„No running away. Come back here, or I‘ll have to add another one.“

Barry grabbed the chair with visibly trembling hands and took a step back again, pulling the chair with him. He seemed unsure of whether to apologize or keep silent, and Len had absolutely no intention of helping him. Barry messing up meant more spanks for him to lay on this perfect butt, after all. And while he prided himself in being a just ruler and master and to not punish senselessly, that did not mean that he had to help Barry in getting as little punishment as possible.

As soon as Barry had taken up position again he lifted the cane again, laying a second welt neatly underneath the first one, perfectly parallel to it, and driving Barry a step forward again. This time, Barry was already moving backwards before Len could point it out to him. Sweet twink probably didn‘t want to earn more strikes, which was a pity, since Len would love to lay down more strikes on that ass. He knew he would get there though, and that he shouldn‘t overdo it on their first day if he wanted to build some kind of trust between him and Barry. And while Barry would be a mere servant to him, he would still be the one to bring Len his food and to care for his things, and he defintely should treat Barry accordingly so he wouldn‘t need to worry about holes in his suit or stomach bugs from bad food. After all, as much as the master had all the power, the servants had many ways of getting back at them, and Len was not keen on risking to experience those.

After the third strike Barry had moved back before Len had finished pulling the cane back up again, and on the forth one, he managed to stay in place even though Len made sure to hit him quite forcefully, and really low on his cheeks.

„You‘re taking it well so far, boy. And it looks so pretty now, all marked up and mine“; Len told him not without pride, and reached out to firmly pat the welts, pointedly ignoring Barry‘s flinch.

„Now, ask me for the last one.“

This time it took a few moments for Barry to respond, but in the end, he hung his head and obediently replied, even though his voice was quiet as he spoke.

„Please Sir, may I get the last strike?“

And of course, Len was only too happy to deliver, cleanly placing the last strike over the first one, causing the welt to crack in one place. Barry gasped in pain at this one and actively flinched away, but he had the good sense not to use his hands to cover his ass, at least. He continued to stand hunched over the chair, breathing deeply and looking very much as if he wanted to pretend not to be in pain. Which very clearly, he was.

Len was a little annoyed with himself, he was usually so good at spankings and canings without ever drawing blood, but he reminded himself that this was a new spankee, some with apparently very tender skin, and everyone was different, so he‘d have to learn how to spank Barry well still.

„You took that very well, boy“ he praised him and stepped forward enough to place a hand on the panting boy‘s hair. „Stand, and come around the desk with me.“

Barry stood stiffly, clearly in pain, but followed Len around the desk without complaints. Really, this one was a gift. Normally, they‘d let servants go if they did a good job, they‘d keep them for a few years and then sent them off with the recommendation of a lifetime and a threat to their lives if they ever breathed a word about what „Winters Ice Company“ really was. But Barry… Barry he might just keep forever if he turned out to be as good as he was thinking now. After all, he‘d taken on a life debt, so it wasn‘t like he would be able to complain about that.

He let himself fall into his comfortable chair and reached into a desk drawer, pulling out a familiar jar with lotion in it. Normally, he‘d just hand it to whoever he‘d just spanked and told them to put some on themselves, but now he dipped his fingers in himself and manhandled Barry around so he was standing with his backside towards Len. He hissed a little the first time the cool lotion touched the welts, but then visibly relaxed, easily allowing Len to spread the soothing ointment over his tortured skin. He left out the part where the welt had split open though and sprayed some antiseptic on that space instead. After all, he didn‘t want to start out with giving his new servant an infected wound and have him unable to serve Len for much too long.

„Keep an eye on this. If it doesn‘t get better, tell me. If you fail to inform me, I‘ll make sure you‘ll regret it. You got that?“ Barry nodded, and then quite unexpectedly turned around to take Len‘s hand and kissing it.

„I will keep you updated, Sir. Thank you for looking after me.“ Anyone else, Len would have given a blue eye for daring to touch him, but with Barry, he found himself fighting not to blush. It just seemed to genuine, coming from him, as if he was truly surprised and grateful that Len would do so much as have a second glance at his welts he‘d just given him. So instead of punching him into next week Len ruffled his hair with a small smile.

„You‘re a good one. I‘ll keep you. Now get dressed again, and I‘ll show you my private quarters. You‘ll serve me there, too.“

He watched Barry shimmy into his clothes again and shook his head at Mick‘s questioning gaze, clearly asking if he should accompany the boss and the new servant to Len‘s quarters. But here, in their hideout, safely tucked away, Len didn‘t need his bodyguard and best friend follow him everywhere. Especially not if he was in the company of sweet, but absolutely harmless Barry Allen.

And if he stepped close and rested a comforting hand on Barry‘s shoulder when he noticed him squirmed when his welts brushed against his clothes, well, no one had to know.

Two months into his service to Len, Barry took a bullet to the shoulder when pushing some idiot out of the way that had pulled a gun on Len in Len‘s own office. Shawna managed to stitch him up again without any lasting effects remaining, but technically, by risking his life to protect Len, Barry had repaid his life debt already.

Leonard Snart made the executive decision not to inform his servant of this fact.


End file.
